Triazolyl disulphides

ABSTRACT

The present invention provides the composition for novel triazolyl disulphides, the acid addition salts and metal salt complexes of the triazolyl disulphides, a process for their preparation, and a method for their use as microbicides.

This is a divisional application of U.S. application Ser. No.09/586,318, filed Jun. 2, 2000, now U.S. Pat. No. 6,245,794, which inturn was a divisional application of U.S. application Ser. No.09/180,325 filed Nov. 5, 1998, now U.S. Pat. No. 6,114,368 which is a371 of PCT/EP97/00282, filed May 5, 1997.

TECHNICAL FIELD OF THE INVENTION

The present invention relates to novel triazolyl disulphides, to aprocess for their preparation and to their use as microbicides.

BACKGROUND OF THE INVENTION

It is already known that numerous triazolyl derivatives have fungicidalproperties (cf. EP-A 0 015 756, EP-A 0 040 345, EP-A 0 052 424, EP-A 0061 835, EP-A 0 297 345, EP-A 0 094 564, EP-A 0 196 038, EP-A 0 267 778,EP-A 0 378 953, EP-A 0 044 605, EP-A 0 069 442, EP-A 0 055 833, EP-A 0301 393, DE-A 2 324 010, DE-A 2 737 489, DE-A 2 551 560, EP-A 0 065 485,DE-A 2 735 872, EP-A 0 234 242, DE-A 2 201 063, EP-A 0 145 294 and DE-A3 721 786). The activity of these compounds is good, but in some casesleaves something to be desired at low application rates.

DETAILED DESCRIPTION OF THE INVENTION

This invention, accordingly, provides novel triazolyl disulphides of theformula

in which

R¹ represents a radical of the formula

 in which

R² and R³ are identical or different and each represents optionallysubstituted alkyl, optionally substituted alkenyl, optionallysubstituted cycloalkyl, optionally substituted aralkyl, optionallysubstituted aralkenyl, optionally substituted aroxyalkyl, optionallysubstituted aryl or optionally substituted heteroaryl, or

R¹ represents a radical of the formula

 in which

R⁴ represents alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1to 4 carbon atoms and 1 to 5 halogen atoms, optionallyhalogen-substituted cycloalkyl having 3 to 7 carbon atoms, naphthyl orrepresents phenyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, nitro, phenyl, phenoxy, alkyl having 1 to 4 carbon atoms,alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbonatoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbonatoms and 1 to 5 halogen atoms and halogenoalkylthio having 1 to 4carbon atoms and 1 to 5 halogen atoms, and

R⁵ represent phenyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5halogen atoms and halogenoalkylthio having 1 to 4 carbon atoms and 1 to5 halogen atoms, or

R¹ represents a radical of the formula

 in which

R⁶ and R⁷ independently of one another each represent hydrogen or alkylhaving 1 to 6 carbon atoms,

X¹ represents halogen, alkyl having 1 to 5 carbon atoms, alkoxy having 1to 4 carbon atoms, phenyl, phenoxy, halogenoalkyl having 1 to 4 carbonatoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbonatoms and 1 to 5 halogen atoms or represents halogenoalkylthio having 1to 4 carbon atoms and 1 to 5 halogen atoms, and

m represents the numbers 0, 1 or 2, or

R¹ represents a radical of the formula

 in which

R⁸ and R⁹ independently of one another each represent hydrogen or alkylhaving 1 to 6 carbon atoms,

X² represents halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms,alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbonatoms and 1 to 5 halogen atoms, halogenoalkoxy having 1 to 4 carbonatoms and 1 to 5 halogen atoms or phenyl,

n represents the numbers 0 or 1 and

p represents the numbers 0, 1 or 2, or

R¹ represents a radical of the formula

 in which

R¹⁰ represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1to 6 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 3 to 6carbon atoms which is optionally substituted by halogen and/or alkylhaving 1 to 4 carbon atoms, optionally substituted aryl or representsoptionally substituted aralkyl, or

R¹ represents a radical of the formula

 in which

R¹¹ represents hydrogen, alkyl or optionally substituted cycloalkyl,

X³ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms,

q represents the numbers 0, 1, 2 or 3 and

Y¹ represents an oxygen atom, a CH₂ group or a direct bond, or

R¹ represents a radical of the formula

 in which

R¹² represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1to 4 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 3 to 7carbon atoms which is optionally substituted by halogen and/or alkylhaving 1 to 4 carbon atoms, cycloalkylalkyl having 3 to 7 carbon atomsin the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety,optionally halogen-substituted phenyl or represents optionallyhalogen-substituted benzyl,

X⁴ represents halogen, nitro, alkyl having 1 to 4 carbon atoms, alkoxyhaving 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms,halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms,halogenoalkylthio having 1 to 4 carbon atoms and 1 to 5 halogen atoms,phenyl which is optionally substituted by halogen and/or alkyl having 1to 4 carbon atoms or represents phenoxy which is optionally substitutedby halogen and/or alkyl having 1 to 4 carbon atoms,

r represents the numbers 0, 1, 2 or 3 and

Y² represents an oxygen atom or represents a CH₂ group, or

R¹ represents a radical of the formula

 in which

A represents alkanediyl having 2 or 3 carbon atoms which is optionallysubstituted by halogen and/or alkyl having 1 to 4 carbon atoms,

X⁵ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms and

s represents the numbers 0, 1, 2 or 3, or

R¹ represents a radical of the formula

 in which

R¹³ represents alkyl having 1 to 10 carbon atoms, halogenoalkyl having 1to 6 carbon atoms and 1 to 5 halogen atoms, fluoroalkoxyalkyl having 1to 4 carbon atoms in the fluoroalkoxy moiety and 1 to 4 carbon atoms inthe alkyl moiety, cycloalkyl having 3 to 7 carbon atoms which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms, cycloalkylalkyl having 3 to 7 carbon atoms in the cycloalkylmoiety and 1 to 4 carbon atoms in the alkyl moiety, optionallyhalogen-substituted phenyl or represents optionally halogen-substitutedphenylalkyl having 1 to 4 carbon atoms in the alkyl moiety,

X⁶ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms, and

t represents the numbers 0, 1, 2 or 3, or

R¹ represents a radical of the formula

 in which

R¹⁴ represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1to 4 carbon atoms and 1 to 5 halogen atoms, cycloalkyl having 3 to 7carbon atoms which is optionally substituted by halogen and/or alkylhaving 1 to 4 carbon atoms, cycloalkylalkyl having 3 to 7 carbon atomsin the cycloalkyl moiety and 1 to 4 carbon atoms in the alkyl moiety,phenyl which is optionally substituted by halogen or represents benzylwhich is optionally substituted by halogen,

X⁷ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms,

u represents the numbers 0, 1, 2 or 3 and

Y³ represents an oxygen atom or represents a CH₂ group, or

R¹ represents a radical of the formula

 in which

R¹⁵ represents alkyl having 1 to 6 carbon atoms, halogenoalkyl having 1to 6 carbon atoms and 1 to 5 halogen atoms, optionally substituted arylor represents optionally substituted aralkyl,

X⁸ represents halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms or represents phenoxy which is optionally substituted by halogenand/or alkyl having 1 to 4 carbon atoms and

v represents the numbers 0, 1, 2 or 3,

and acid addition salts and metal salt complexes thereof.

A large number of the substances according to the invention contain oneor more asymmetrically substituted carbon atoms. They may therefore beobtained in the form of optical isomers. The present invention relatesboth to the individual isomers and to mixtures thereof.

Furthermore, it has been found that triazolyl disulphides of the formula(I) and acid addition salts and metal salt complexes thereof areobtained when mercaptotriazoles of the formula

in which

R¹ is as defined above

are reacted with weak oxidizing agents in the presence of a diluent and,if appropriate, an acid or a metal salt is subsequently added to theresulting compounds of the formula (I).

Finally, it has been found that the novel triazolyl disulphides of theformula (I) and acid addition salts and metal salt complexes thereofhave very good microbicidal properties and can be used both in cropprotection and in the protection of materials for controllingundesirable microorganisms.

Surprisingly, the substances according to the invention have bettermicrobicidal activity, in particular fungicidal activity, than theconstitutionally most similar compounds of the prior art which have thesame direction of action.

The formula (I) provides a general definition of the triazolyldisulphides according to the invention.

R¹ preferably represents a radical of the formula

 in which

R² preferably represents straight-chain or branched alkyl having 1 to 6carbon atoms, it being possible for these radicals to be mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of halogen, alkoxy having 1 to 4 carbon atoms,alkoximino having 1 to 4 carbon atoms in the alkoxy moiety andcycloalkyl having 3 to 7 carbon atoms, or

preferably represents straight-chain or branched alkenyl having 2 to 6to carbon atoms, it being possible for each of these radicals to bemono- to trisubstituted by identical or different substituents selectedfrom the group consisting of halogen, alkoxy having 1 to 4 carbon atomsand cycloalkyl having 3 to 7 carbon atoms, or

preferably represents cycloalkyl having 3 to 7 carbon atoms, it beingpossible for each of these radicals to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, cyano and alkyl having 1 to 4 carbon atoms, or

preferably represents aralkyl having 6 to 10 carbon atoms in the arylmoiety and 1 to 4 carbon atoms in the straight-chain or branched alkylmoiety, it being possible for the aryl moiety to be in each case mono-to trisubstituted by identical or different substituents selected fromthe group consisting of halogen, alkyl having 1 to 4 carbon atoms,alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenalkoxy having 1 or 2 carbon atoms and 1to 5 identical or different halogen atoms, halogenoalkylthio having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety, nitro and cyano, or

preferably represents aralkenyl having 6 to 10 carbon atoms in the alkylmoiety and 2 to 4 carbon atoms in the alkenyl moiety, it being possiblefor the aryl moiety to be in each case mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand cyano, or

preferably represents aroxyalkyl having 6 to 10 carbon atoms in the arylmoiety and 1 to 4 carbon atoms in the straight-chain or branchedoxyalkyl moiety, it being possible for the aryl moiety to be in eachcase mono- to trisubstituted by identical or different substituentsselected from the group consisting of halogen, alkyl having 1 to 4carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, halogenoalkoxy having 1 or 2carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl,phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety,alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to4 carbon atoms in the alkyl moiety, nitro and cyano, or

preferably represents aryl having 6 to 10 carbon atoms, it beingpossible for each of these radicals to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand cyano, or

preferably represents an optionally benzo-fused 5- or 6-memberedheteroaromatic radical having 1 to 3 hetero atoms, such as nitrogen,sulphur and/or oxygen, it being possible for each of these radicals tobe mono- to trisubstituted by identical or different substituentsselected from the group consisting of halogen, alkyl having 1 to 4carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, hydroxyalkinylhaving 3 to 8 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthiohaving 1 or 2 carbon atoms, halogenoalkyl, halogenoalkoxy andhalogenoalkylthio having in each case 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, such as fluorine or chlorineatoms, formyl, dialkoxymethyl having 1 or 2 carbon atoms in each alkoxygroup, acyl having 2 to 4 carbon atoms, alkoxycarbonyl having 1 to 4carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbonatoms in the alkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety,nitro and cyano, and

R³ preferably represents straight-chain or branched alkyl having 1 to 6carbon atoms, it being possible for these radicals to be mono- totetrasubstituted by identical or different substituents selected fromthe group consisting of halogen, alkoxy having 1 to 4 carbon atoms,alkoximino having 1 to 4 carbon atoms in the alkoxy moiety andcycloalkyl having 3 to 7 carbon atoms, or

preferably represents straight-chain or branched alkenyl having 2 to 6carbon atoms, it being possible for each of these radicals to be mono-to trisubstituted by identical or different substituents selected fromthe group consisting of halogen, alkoxy having 1 to 4 carbon atoms andcycloalkyl having 3 to 7 carbon atoms, or

preferably represents cycloalkyl having 3 to 7 carbon atoms, it beingpossible for each of these radicals to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, cyano and alkyl having 1 to 4 carbon atoms, or

preferably represents aralkyl having 6 to 10 carbon atoms in the arylmoiety and 1 to 4 carbon atoms in the straight-chain or branched alkylmoiety, it being possible for the aryl moiety to be in each case mono-to trisubstituted by identical or different substituents selected fromthe group consisting of halogen, alkyl having 1 to 4 carbon atoms,alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms,halogenoalkyl having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkoxy having 1 or 2 carbon atoms and 1to 5 identical or different halogen atoms, halogenoalkylthio having 1 or2 carbon atoms and 1 to 5 identical or different halogen atoms,cycloalkyl having 3 to 7 carbon atoms, phenyl, phenoxy, alkoxycarbonylhaving 1 to 4 carbon atoms in the alkoxy moiety, alkoximinoalkyl having1 to 4 carbon atoms in the alkoxy moiety and 1 to 4 carbon atoms in thealkyl moiety, nitro and cyano, or

preferably represents aralkenyl having 6 to 10 carbon atoms in the arylmoiety and 2 to 4 carbon atoms in the alkenyl moiety, it being possiblefor the aryl moiety to be in each case mono- to trisubstituted byidentical or different substituents from the group consisting ofhalogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbonatoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand cyano, or

preferably represents aroxyalkyl having 6 to 10 carbon atoms in the arylmoiety and 1 to 4 carbon atoms in the straight-chain or branchedoxyalkyl moiety, it being possible for the aryl moiety to be in eachcase mono- to trisubstituted by identical or different substituentsselected from the group consisting of halogen, alkyl having 1 to 4carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4carbon atoms, halogenoalkyl having 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, halogenoalkoxy having 1 or 2carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkylthio having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, cycloalkyl having 3 to 7 carbon atoms, phenyl,phenoxy, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety,alkoximinoalkyl having 1 to 4 carbon atoms in the alkoxy moiety and 1 to4 carbon atoms in the alkyl moiety, nitro and cyano, or

preferably represents aryl having 6 to 10 carbon atoms, it beingpossible for each of these radicals to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkyl having1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms,halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 identical ordifferent halogen atoms, halogenoalkylthio having 1 or 2 carbon atomsand 1 to 5 identical or different halogen atoms, cycloalkyl having 3 to7 carbon atoms, phenyl, phenoxy, alkoxycarbonyl having 1 to 4 carbonatoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbon atomsin the alkoxy moiety and 1 to 4 carbon atoms in the alkyl moiety, nitroand cyano, or

preferably represents an optionally benzo-fused 5- or 6-memberedheteroaromatic radical having 1 to 3 hetero atoms, such as nitrogen,sulphur and/or oxygen, it being possible for each of these radicals tobe mono- to trisubstituted by identical or different substituentsselected from the group consisting of halogen, alkyl having 1 to 4carbon atoms, hydroxyalkyl having 1 to 4 carbon atoms, hydroxyalkinylhaving 3 to 8 carbon atoms, alkoxy having 1 or 2 carbon atoms, alkylthiohaving 1 or 2 carbon atoms, halogenoalkyl, halogenoalkoxy andhalogenoalkylthio having in each case 1 or 2 carbon atoms and 1 to 5identical or different halogen atoms, such as fluorine or chlorineatoms, formyl, dialkoxymethyl having 1 or 2 carbon atoms in each alkoxygroup, acyl having 2 to 4 carbon atoms, alkoxycarbonyl having 1 to 4carbon atoms in the alkoxy moiety, alkoximinoalkyl having 1 to 4 carbonatoms in the alkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety,nitro and cyano.

R¹ furthermore preferably represents a radical of the formula

 in which

R⁴ preferably represents methyl, ethyl, n-propyl, isopropyl, n-butyl,sec-butyl, isobutyl, tert-butyl, fluoro-tert-butyl, difluoro-tert-butyl,cycloalkyl having 3 to 6 carbon atoms which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine and bromine, represents naphthylor represents phenyl which may be mono- to trisubstituted by identicalor different substituents selected from the group consisting offluorine, chlorine, bromine, nitro, phenyl, phenoxy, methyl, ethyl,tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl,difluoromethyl, difluorochloromethyl, trifluoromethoxy, difluoromethoxyand trifluoromethylthio, and

R⁵ preferably represents phenyl which may be mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl,methoxy, ethoxy, trifluoromethyl, trichloromethyl, difluoromethyl,difluorochloromethyl, trifluoromethoxy, difluoromethoxy andtrifluoromethylthio.

R¹ furthermore preferably represents a radical of the formula

 in which

R⁶ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

R⁷ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

X¹ preferably represents fluorine, chlorine, bromine, methyl, ethyl,n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, methoxy,ethoxy, phenyl, phenoxy, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy or trifluoromethylthio and

m also preferably represents the numbers 0, 1 or 2,

it being possible for X¹ to represent identical or different radicals ifm represents 2.

R¹ furthermore preferably represents a radical of the formula

 in which

R⁸ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

R⁹ preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

X² preferably represents fluorine, chlorine, bromine, cyano, nitro,methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl,tert-butyl, methoxy, ethoxy, trifluoromethyl, trichloromethyl,difluoromethyl, trichloromethoxy, trifluoromethoxy, difluoromethoxy,difluorochloromethoxy or phenyl,

n also preferably represents the numbers 0 or 1 and

p also preferably represents the numbers 0, 1 or 2,

it being possible for X² to represent identical or different radicals ifp represents 2.

R¹ furthermore preferably represents a radical of the formula

 in which

R¹⁰ preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, straight-chain or branched halogenoalkyl having 1 to 4carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,represents cycloalkyl having 3 to 6 carbon atoms which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine, bromine, methyl andethyl, represents phenyl, benzyl or phenethyl, it being possible foreach of the three last-mentioned radicals to be mono- to trisubstitutedby identical or different substituents selected from the groupconsisting of halogen, alkyl having 1 to 4 carbon atoms, alkoxy having 1to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkoxyhaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, halogenoalkylthiohaving 1 to 4 carbon atoms and 1 to 5 halogen atoms, phenyl which isoptionally substituted by halogen and/or alkyl having 1 to 4 carbonatoms or phenoxy which is optionally substituted by halogen and/or alkylhaving 1 to 4 carbon atoms.

R¹ furthermore preferably represents a radical of the formula

 in which

R¹¹ preferably represents hydrogen, straight-chain or branched alkylhaving 1 to 12 carbon atoms or represents cycloalkyl having 3 to 7carbon atoms which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen andalkyl having 1 to 4 carbon atoms,

X³ preferably represents fluorine, chlorine, bromine, methyl, ethyl,methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy,difluoromethoxy, trifluoromethylthio, phenyl or phenoxy,

q preferably represents the numbers 0, 1, 2 or 3, it being possible forX³ to represent identical or different radicals if q represents 2 or 3,and

Y¹ preferably represents an oxygen atom, a CH₂ group or a direct bond.

R¹ furthermore preferably represents a radical of the formula

 in which

R¹² preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, fluoroalkyl having 1 to 4 carbon atoms and 1 to 5 fluorineatoms, cycloalkyl having from 3 to 6 carbon atoms which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine, bromine, methyl andethyl, cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkylmoiety and 1 to 3 carbon atoms in the alkyl moiety, phenyl which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand bromine or represents benzyl which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine and bromine,

X⁴ preferably represents fluorine, chlorine, bromine, nitro, methyl,ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl which is optionally mono- or disubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine and methyl or represents phenoxy which is optionallymono- or disubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine, bromine and methyl,

r preferably represents the numbers 0, 1, 2 or 3, it being possible forX⁴ to represent identical or different radicals if r represents 2 or 3and

Y² preferably represents an oxygen atom or represents a CH₂ group.

R¹ furthermore preferably represents a radical of the formula

 in which

A preferably represents alkanediyl having 2 or 3 carbon atoms which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl, sec-butyland tert-butyl,

X⁵ preferably represents fluorine, chlorine, bromine, methyl, ethyl,methoxy, methylthio, trichloromethyl, trifluoromethyl, trifluoromethoxy,trifluoromethylthio, difluoromethoxy, phenyl which is optionally mono-totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine and methyl or phenoxy which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand methyl and

s preferably represents the numbers 0, 1, 2 or 3, it being possible forX⁵ to represent identical or different radicals if s represents 2 or 3.

R¹ furthermore preferably represents a radical of the formula

 in which

R¹³ preferably represents straight-chain or branched alkyl having 1 to 6carbon atoms, straight-chain or branched halogenoalkyl having 1 to 6carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms,fluoroalkoxyalkyl having 1 to 3 carbon atoms and 1 to 5 fluorine atomsin the fluoroalkoxy moiety and 1 to 3 carbon atoms in the alkyl moiety,cycloalkyl having 3 to 6 carbon atoms which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl and ethyl,cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and1 to 3 carbon atoms in the alkyl moiety, phenyl which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine and bromine orrepresents phenylalkyl having 1 or 2 carbon atoms in the alkyl moietywhich is optionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand bromine,

X⁶ preferably represents fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which isoptionally mono- or disubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine andmethyl or represents phenoxy which is optionally mono- or disubstitutedby identical or different substituents selected from the groupconsisting of fluorine, chlorine, bromine and methyl and

t preferably represents the numbers 0, 1, 2 or 3, it being possible forX⁶ to represent identical or different radicals if t represents 2 or 3.

R¹ furthermore preferably represents a radical of the formula

 in which

R¹⁴ preferably represents straight-chain or branched alkyl having 1 to 4carbon atoms, fluoroalkyl having 1 to 4 carbon atoms and 1 to 5 fluorineatoms, cycloalkyl having 3 to 6 carbon atoms which is optionally mono-to trisubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, methyl and ethyl,cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and1 to 3 carbon atoms in the alkyl moiety, phenyl which is optionallymono- to trisubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine and bromine orrepresents benzyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine and bromine,

X⁷ preferably represents fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which isoptionally mono- or disubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine andmethyl or represents phenoxy which is optionally mono- or disubstitutedby identical or different substituents selected from the groupconsisting of fluorine, chlorine, bromine and methyl,

u preferably represents the numbers 0, 1, 2 or 3, it being possible forX⁷ to represent identical or different radicals if u represents 2 or 3,and

Y³ preferably represents an oxygen atom or represents a CH₂ group.

R¹ furthermore also preferably represents a radical of the formula

 in which

R¹⁵ preferably represents a straight-chain or branched alkyl having 1 to4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5halogen atoms, phenyl which is optionally mono- to trisubstituted byidentical or different substituents selected from the group consistingof halogen, alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 or2 carbon atoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbonatoms and halogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 halogenatoms or represents phenylalkyl having 1 to 4 carbon atoms in the alkylmoiety which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of halogen,alkyl having 1 to 4 carbon atoms, halogenoalkyl having 1 or 2 carbonatoms and 1 to 5 halogen atoms, alkoxy having 1 to 4 carbon atoms andhalogenoalkoxy having 1 or 2 carbon atoms and 1 to 5 halogen atoms,

X⁸ preferably represents fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl which isoptionally mono- or disubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine andmethyl or represents phenoxy which is optionally mono- or disubstitutedby identical or different substituents selected from the groupconsisting of fluorine, chlorine, bromine and methyl and

v preferably represents the numbers 0, 1, 2 or 3, it being possible forX⁸ to represent identical or different radicals if v represents 2 or 3.

R¹ particularly preferably represents a radical of the formula

 in which

R² particularly preferably represents straight-chain or branched alkylhaving 1 to 4 carbon atoms, it being possible for these radicals to bemono- to tetrasubstituted by identical or different substituents fromthe group consisting of fluorine, chlorine, bromine, methoxy, ethoxy,propoxy, isopropoxy, alkoximino having 1 or 2 carbon atoms in the alkoxymoiety, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, or

particularly preferably represents straight-chain or branched alkenylhaving 2 to 5 carbon atoms, it being possible for each of these radicalsto be mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methoxy, ethoxy, propoxy, isopropoxy, cyclopropyl, cyclobutyl,cyclopentyl and cyclohexyl, or

particularly preferably represents cycloalkyl having 3 to 6 carbonatoms, it being possible for each of these radicals to be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, cyano, methyl, ethyl,propyl, isopropyl and tert-butyl, or

particularly preferably represents phenylalkyl having 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, it being possiblefor the phenyl moiety to be mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy,methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio,methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl,nitro and cyano, or

particularly preferably represents phenylalkenyl having 2 to 4 carbonatoms in the alkenyl moiety, it being possible for the phenyl moiety tobe mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,or

particularly preferably represents phenoxyalkyl having 1 to 4 carbonatoms in the straight-chain or branched oxyalkyl moiety, it beingpossible for the phenyl moiety to be mono- trisubstituted by identicalor different substituents selected from the group consisting offluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy,methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio,methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl,nitro and cyano, or

particularly preferably represents phenyl which may be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, to methoximinomethyl, 1-methoximinoethyl, nitro andcyano, or

particularly preferably represents pyrazolyl, imidazolyl,1,2,4-triazolyl, pyrrolyl, furanyl, thienyl, thiazolyl, oxazolyl,pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl,quinazolinyl, indolyl, benzothienyl, benzofuranyl, benzothiazolyl orbenzimidazolyl, it being possible for each of these radicals to be mono-to trisubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,chlorodifluoromethylthio, hydroxymethyl, hydroxyethyl, hydroxyalkinylhaving 4 to 6 carbon atoms, methoxycarbonyl, ethoxycarbonyl,methoximinomethyl, 1-methoximinoethyl, nitro and/or cyano, formyl,dimethoxymethyl, acetyl and propionyl, and

R³ particularly preferably represents straight-chain or branched alkylhaving, 1 to 4 carbon atoms, it being possible for these radicals to bemono- to tetrasubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methoxy, ethoxy, propoxy, isopropoxy, alkoximino having 1 or 2 carbonatoms in the alkoxy moiety, cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl, or

particularly preferably represents straight-chain or branched alkenylhaving 2 to 5 carbon atoms, it being possible for each of these radicalsto be mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methoxy, ethoxy, propoxy, isopropoxy, cyclopropyl, cyclobutyl,cyclopentyl and cyclohexyl, or

particularly preferably represents cycloalkyl having 3 to 6 carbonatoms, it being possible for each of these radicals to be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, cyano, methyl, ethyl,propyl, isopropyl and tert-butyl, or

particularly preferably represents phenylalkyl having 1 to 4 carbonatoms in the straight-chain or branched alkyl moiety, it being possiblefor the phenyl moiety to be mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, ethyl, tert-butyl, methoxy, ethoxy,methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio,chlorodifluoromethoxy, difluoromethoxy, chlorodifluoromethylthio,methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl,nitro and cyano, or

particularly preferably represents phenylalkenyl having 2 to 4 carbonatoms in the alkenyl moiety, it being possible for the phenyl moiety tobe mono- to trisubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,or

particularly preferably represents phenoxyalkyl having 1 to 4 carbonatoms in the straight-chain or branched oxyalkyl moiety, it beingpossible for the phenyl moiety to be mono- to trisubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, methyl, ethyl, tert-butyl, methoxy,ethoxy, methylthio, trifluoromethyl, trifluoromethoxy,trifluoromethylthio, chlorodifluoromethoxy, difluoromethoxy,chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl,methoximinomethyl, 1-methoximinoethyl, nitro and cyano, or

particularly preferably represents phenyl which may be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,difluoromethoxy, chlorodifluoromethylthio, methoxycarbonyl,ethoxycarbonyl, methoximinomethyl, 1-methoximinoethyl, nitro and cyano,or

particularly preferably represents pyrazolyl, imidazolyl,1,2,4-triazolyl, pyrrolyl, furanyl, thienyl, thiazolyl, oxazolyl,pyridinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl,quinazolinyl, indolyl, benzothienyl, benzofuranyl, benzothiazolyl orbenzimidazolyl, it being possible for each of these radicals to be mono-to trisubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, methyl, ethyl,tert-butyl, methoxy, ethoxy, methylthio, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, chlorodifluoromethoxy,chlorodifluoromethylthio, hydroxymethyl, hydroxyethyl, hydroxyalkinylhaving 4 to 6 carbon atoms, methoxycarbonyl, ethoxycarbonyl,methoximinomethyl, 1-methoximinoethyl, nitro and/or cyano, formyl,dimethoxymethyl, acetyl and propionyl.

R¹ furthermore particularly preferably represents a radical of theformula

 in which

R⁴ particularly preferably represents methyl, ethyl, n-propyl,isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, fluoro-tert-butyl,difluoro-tert-butyl, cycloalkyl having 3 to 6 carbon atoms which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand bromine, represents naphthyl or represents phenyl which may be mono-to trisubstituted by identical or different substituents selected fromthe group consisting of fluorine, chlorine, bromine, nitro, phenyl,phenoxy, methyl, ethyl, tert-butyl, methoxy, ethoxy, trifluoromethyl,trichloromethyl, difluoromethyl, difluorochloromethyl, trifluoromethoxy,difluoromethoxy and trifluoromethylthio, and

R⁵ particularly preferably represents phenyl which may be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl, ethyl,isopropyl, tert-butyl, methoxy, ethoxy, trifluoromethyl,trichloromethyl, difluoromethyl, difluorochloromethyl, trifluoromethoxy,difluoromethoxy and trifluoromethylthio.

R¹ furthermore particularly preferably represents a radical of theformula

 in which

R⁶ particularly preferably represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

R⁷ particularly preferably represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

X¹ particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl,tert-butyl, methoxy, ethoxy, phenyl, phenoxy, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy ortrifluoromethylthio and

m also particularly preferably represents the numbers 0, 1 or 2,

where X¹ may represent identical or different radicals if m represents2.

R¹ furthermore particularly preferably represents a radical of theformula

 in which

R⁸ particularly preferably represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

R⁹ particularly preferably represents hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or n-pentyl,

X² particularly preferably represents fluorine, chlorine, bromine,cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl,sec-butyl, tert-butyl, methoxy, ethoxy, trifluoromethyl,trichloromethyl, difluoromethyl, trichloromethoxy, trifluoromethoxy,difluoromethoxy, difluorochloromethoxy or phenyl,

n also particularly preferably represents the numbers 0 or 1 and

p also particularly preferably represents the numbers 0, 1 or 2,

it being possible for X² to represent identical or different radicals ifp represents 2.

R¹ furthermore particularly preferably represents a radical of theformula

 in which

R¹⁰ particularly preferably represents methyl, ethyl, n-propyl,isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 3 fluorine, chlorine and/or bromineatoms, cyclopropyl, cyclopentyl or cyclohexyl, each of which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, methyl and ethyl, and also represents phenyl, benzyl orphenethyl, where each of the three last-mentioned radicals may be mono-to trisubstituted in the phenyl moiety by identical or differentsubstituents selected from the group consisting of fluorine, chlorine,bromine, methyl, ethyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl and phenoxy.

R¹ furthermore particularly preferably represents a radical of theformula

 in which

R¹¹ particularly preferably represents hydrogen, straight-chain orbranched alkyl having 1 to 6 carbon atoms or represents cyclopropyl,cyclopentyl or cyclohexyl, each of which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine, bromine, methyl and ethyl,

X³ particularly preferably represents fluorine, chlorine, bromine,methyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, difluoromethoxy, trifluoromethylthio, phenyl orphenoxy,

q also particularly preferably represents the numbers 0, 1, 2 or 3, itbeing possible for X³ to represent identical or different radicals if qrepresents 2 or 3 and

Y¹ also particularly preferably represents an oxygen atom, a CH₂ groupor a direct bond.

R¹ furthermore particularly preferably represents a radical of theformula

 in which

R¹² particularly preferably represents methyl, isopropyl, tert-butyl,fluoro-tert-butyl, difluoro-tert-butyl, represents cyclopropyl,cyclopentyl or cyclohexyl, each of which may optionally be mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine and methyl, representscycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and1 or 2 carbon atoms in the alkyl moiety, phenyl which is optionallymono- or disubstituted by identical or different substituents selectedfrom the group consisting of fluorine, chlorine and bromine orrepresents benzyl which is optionally mono- or disubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine and bromine,

X⁴ particularly preferably represents fluorine, chlorine, bromine,nitro, methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy,

r also particularly preferably represents the numbers 0, 1 2 or 3, itbeing possible for X⁴ to represent identical or different radicals if rrepresents 2 or 3 and

Y² also particularly preferably represents an oxygen atom or representsa CH₂ group.

R¹ furthermore particularly preferably represents a radical of theformula

 in which

A particularly preferably represents alkanediyl having 2 or 3 carbonatoms which is optionally mono- to trisubstituted by identical ordifferent substituents selected from the group consisting of fluorine,chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, n-butyl, i-butyl,sec-butyl and tert-butyl,

X⁵ particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, methoxy, methylthio, trichloromethyl, trifluoromethyl,trifluoromethoxy, trifluoromethylthio, difluoromethoxy, phenyl which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand methyl and/or represents phenoxy which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine and methyl and

s also particularly preferably represents the numbers 0, 1, 2 or 3, itbeing possible for X⁵ to represent identical or different radicals if srepresents 2 or 3.

R¹ furthermore particularly preferably represents a radical of theformula

 in which

R¹³ particularly preferably represents methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, halogenoalkylhaving 1 to 4 carbon atoms and 1 to 5 fluorine, chlorine and/or bromineatoms, fluoroalkoxyalkyl having 1 or 2 carbon atoms and 1 to 5 fluorineatoms in the fluoroalkoxy moiety and 1 or 2 carbon atoms in tile alkylmoiety, cyclopropyl, cyclopentyl or cyclohexyl, each of which isoptionally mono- to trisubstituted by identical or differentsubstituents selected from the group consisting of fluorine, chlorineand methyl, represents cycloalkylalkyl having 3 to 6 carbon atoms in thecycloalkyl moiety and 1 or 2 carbon atoms in the alkyl moiety,represents phenyl which is optionally mono- or disubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine and bromine or represents benzyl which isoptionally mono- or disubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine and bromine,

X⁶ particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy and

t also particularly preferably represents the numbers 0, 1, 2 or 3, itbeing possible for X⁶ to represent identical or different radicals if trepresents 2 or 3.

R¹ furthermore particularly preferably represents a radical of theformula

 in which

R¹⁴ particularly preferably represents methyl, isopropyl, tert-butyl,fluoro-tert-butyl, difluoro-tert-butyl, represents cyclopropyl,cyclopentyl or cyclohexyl, each of which is optionally mono- totrisubstituted by identical or different substituents selected from thegroup consisting of fluorine, chlorine and methyl, representscycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moiety and1 or 2 carbon atoms in the alkyl moiety, represents phenyl which isoptionally mono- or disubstituted by identical or different substituentsselected from the group consisting of fluorine, chlorine and bromine orrepresents benzyl which is optionally mono- or disubstituted byidentical or different substituents selected from the group consistingof fluorine, chlorine and bromine,

X⁷ particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy,

Y³ also particularly preferably represents an oxygen atom or representsa CH₂ group, and

u also particularly preferably represents the numbers 0, 1, 2 or 3, itbeing possible for X⁷ to represent identical or different radicals if urepresents 2 or 3.

R¹ moreover also preferably represents a radical of the formula

 in which

R¹⁵ particularly preferably represents methyl, ethyl, n-propyl,isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, fluoro-tert-butyl,difluoro-tert-butyl, phenyl which is optionally mono- or disubstitutedby identical or different substituents selected from the groupconsisting of fluorine, chlorine, methyl, ethyl, trifluoromethyl,trichloromethyl, methoxy, ethoxy, trifluoromethoxy and difluoromethoxyor represents phenylalkyl having 1 or 2 carbon atoms in the alkyl moietywhich is optionally mono- or disubstituted in the phenyl moiety byidentical or different substituents selected from the group consistingof fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl,trichloromethyl, methoxy, ethoxy, trifluoromethoxy and difluoromethoxy,p2 X⁸ particularly preferably represents fluorine, chlorine, bromine,methyl, ethyl, tert-butyl, methoxy, methylthio, trichloromethyl,trifluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio,phenyl or phenoxy, and

v also particularly preferably represents the numbers 0, 1, 2 or 3, itbeing possible for X⁸ to represent identical or different radicals if vrepresents 2 or 3.

Preferred compounds according to the invention are also additionproducts of acids and those triazolyl disulphides of the formula (I) inwhich R¹ has the meanings which have been mentioned as beingparticularly preferred for these substituents.

The acids which can be added preferably include hydrohalic acids, suchas, for example, hydrochloric acid and hydrobromic acid, in particularhydrochloric acid, furthermore phosphoric acid, nitric acid, mono- andbifunctional carboxylic acids and hydroxycarboxylic acids, such as, forexample, acetic acid, maleic acid, succinic acid, fumaric acid, tartaricacid, citric acid, salicylic acid, sorbic acid and lactic acid, and alsosulfonic acids, such as, for example, p-toluenesulfonic acid and1,5-naphthalenedisulphonic acid, and also saccharin and thiosaccharin.

Preferred compounds according to the invention are moreover additionproducts of salts of metals of main groups II to IV and of subgroups Iand II and also IV to VIII of the Periodic Table of the Elements andthose triazolyl disulphides of the formula (I) in which R¹ has themeanings which have already been mentioned as preferred for thesesubstituents.

Particular preference is given here to salts of copper, zinc, manganese,magnesium, tin, iron and nickel. Suitable anions of these salts are theanions derived from those acids which lead to physiologically acceptableaddition products. In this context, particularly preferred acids of thiskind are hydrohalic acids, such as, for example, hydrochloric acid andhydrobromic acid, furthermore phosphoric acid, nitric acid and sulphuricacid.

The mercapto-triazoles required as starting materials for preparing thesubstances according to the invention can be present in the “mercapto”form of the formula

or in the tautomeric “thiono” form of the formula

For simplicity, only the structure of the “mercapto” form is stated ineach case. The substances according to the invention are derived fromthe “mercapto” form.

Examples of substances according to the invention are the triazolyldisulphides listed in the tables below.

TABLE 1 (Ia)

R² R³

—C(CH₃)₃

—C(CH₃)₃

—C(CH₃)₃

—C₄H₉-n

—C(CH₃)₃ Cl₂CH—CCl₂—CH₂— —C(CH₃)₃ Cl₂C═CCl—CH₂—

Cl₂CH—CCl₂—CH₂—

Cl₂CH—CCl₂—CH₂—

—C(CH₃)₃

Cl₂CH—CCl₂—

—C(CH₃)₃

—C(CH₃)₃

TABLE 2 (Ib)

R⁴ R⁵

—CH₃

—CH₃

—CH₃

—C(CH₃)₃

TABLE 3 (Ic)

R⁶ R⁷ X¹ _(m) —CH₃ —CH₃ 4-Br —CH₃ —CH₃ 4-F —CH₃ —CH₃ 2,4-Cl₂ —CH₃ H 4-Cl—CH₃ —CH₃ — —CH₃ —CH₃ 4-CH₃ —CH₃ —CH₃ 2-F, 4-Cl —C₂H₅ H 4-Cl —C₂H₅ —C₂H₅4-Cl —C₃H₇-n H 4-Cl —C₂H₅ H 2,4-Cl₂ —C₂H₅ H 4-F —C₂H₅ H 4-Br —C₂H₅ H

—C₂H₅ H 4-C₄H₉-t —C₃H₇-i H 4-Cl —C₅H₁₁-n H 4-Cl —CH₃ —CH₃

—CH₃ —CH₃ 4-C₄H₉-t —C₄H₉-n H 4-Cl —C₄H₉-i H 4-Cl —CH₃ —C₂H₅ 4-Cl —CH₃—CH₃ 2-Cl —CH₃ —CH₃ 2,3-Cl₂ —CH₃ —CH₃ 4-CF₃ —CH₃ —CH₃ 4-OCF₃ —CH₃ —CH₃4-Cl

TABLE 4 (Id)

R⁸ R⁹ X² _(p) n —CH₃ —CH₃ 4-Br 0 —CH₃ —CH₃ 4-F 0 —CH₃ —CH₃ 2,4-Cl₂ 0—CH₃ H 4-Cl 0 —CH₃ —CH₃ — 0 —CH₃ —CH₃ 4-CH₃ 0 —CH₃ —CH₃ 2-F, 4-Cl 0—C₂H₅ H 4-Cl 0 —C₂H₅ —C₂H₅ 4-Cl 0 —C₃H₇-n H 4-Cl 0 —C₂H₅ H 2,4-Cl₂ 0—C₂H₅ H 4-F 0 —C₂H₅ H 4-Br 0 —C₂H₅ H 4-NO₂ 0 —C₂H₅ H 4-C₄H₉-t 0 —C₃H₇-iH 4-Cl 0 —C₅H₁₁-n H 4-Cl 0 —CH₃ —CH₃ 4-CN 0 —CH₃ —CH₃ 4-C₄H₉-t 0 —C₄H₉-nH 4-Cl 0 —C₄H₉-i H 4-Cl 0 —CH₃ —C₂H₅ 4-Cl 0 —CH₃ —CH₃ 4-Cl 0 —CH₃ —CH₃4-OCH₃ 0 —CH₃ —CH₃ 2-OCH₃ 0 —CH₃ —CH₃ 2-CF₃ 0 —CH₃ —CH₃ 4-CF₃ 0 —CH₃—CH₃ 2-OCF₃ 0 —CH₃ —CH₃ 2-OCHF₂ 0 —CH₃ —CH₃ 4-OCF₃ 0 —CH₃ —CH₃ 4-Br 1—CH₃ —CH₃ 4-F 1 —CH₃ —CH₃ 2,4-Cl₂ 1 —CH₃ H 4-Cl 1 —CH₃ —CH₃ — 1 —CH₃—CH₃ 4-CH₃ 1 —CH₃ —CH₃ 2-F, 4-Cl 1 —C₂H₅ H 4-Cl 1 —C₂H₅ —C₂H₅ 4-Cl 1—C₃H₇-n H 4-Cl 1 —C₂H₅ H 2,4-Cl₂ 1 —C₂H₅ H 4-F 1 —C₂H₅ H 4-Br 1 —C₂H₅ H4-NO₂ 1 —C₂H₅ H 4-C₄H₉-t 1 —C₃H₇-i H 4-Cl 1 —C₅H₁₁-n H 4-Cl 1 —CH₃ —CH₃4-CN 1 —CH₃ —CH₃ 4-C₄H₉-t 1 —C₄H₉-n H 4-Cl 1 —CH₃ —CH₃ 4-Cl 1 —C₄H₉-i H4-Cl 1 —CH₃ —C₂H₅ 4-Cl 1 —CH₃ —CH₃ 4-OCH₃ 1 —CH₃ —CH₃ 2-OCH₃ 1 —CH₃ —CH₃2-CF₃ 1 —CH₃ —CH₃ 4-CF₃ 1 —CH₃ —CH₃ 2-OCF₃ 1 —CH₃ —CH₃ 2-OCHF₂ 1 —CH₃—CH₃ 4-OCF₃ 1 —CH₃ —CH₃ 2-Cl 0 —CH₃ —CH₃ 2,3-Cl₂ 0 —CH₃ —CH₃ 2-Cl 1

TABLE 5 (Ie)

R¹⁰

—C₄H₉-n —C(CH₃)₃ —CH(CH₃)₂

—CH₂—CH(CH₃)₂

TABLE 6 (If)

X³ _(q) Y¹ R¹¹ 4-Cl CH₂ H 4-CF₃ CH₂ H 4-OCF₃ CH₂ H 2,4-Cl₂ CH₂ H 4-CH₃CH₂ H 2-Cl CH₂ H 2-F CH₂ H 4-F CH₂ H 2-OCHF₂ CH₂ H 4-Cl O H 4-CF₃ O H4-OCF₃ O H 2,4-Cl₂ O H 4-CH₃ O H 2-Cl O H 2-F O H 4-F O H 2-OCHF₂ O H4-Cl — H 4-CF₃ — H 4-OCF₃ — H 2,4-Cl₂ — H 4-CH₃ — H 2-Cl — H 2-F — H 4-F— H 2-OCHF₂ — H 4-Cl CH₂ —CH₃ 4-CF₃ CH₂ —CH₃ 4-OCF₃ CH₂ —CH₃ 2,4-Cl₂ CH₂—CH₃ 4-CH₃ CH₂ —CH₃ 2-Cl CH₂ —CH₃ 2-F CH₂ —CH₃ 4-F CH₂ —CH₃ 2-OCHF₂ CH₂—CH₃ 4-Cl O —CH₃ 4-CF₃ O —CH₃ 2,4-Cl₂ O —CH₃ 4-OCF₃ O —CH₃ 2-F O —CH₃2-OCHF₂ O —CH₃ 4-Cl — —CH₃ 4-CF₃ — —CH₃ 2,4-Cl₂ — —CH₃ 4-OCF₃ — —CH₃ 2-F— —CH₃ 2-OCHF₂ — —CH₃ 4-Cl CH₂ C₄H₉-n 2,4-Cl₂ CH₂ —CH(CH₃)₂ 4-OCF₃ CH₂—C(CH₃)₃ 4-Cl CH₂

4-Cl CH₂

4-Cl CH₂

4-Cl CH₂

2,4,6-Cl₃ CH₂ —CH₃

CH₂ —CH₃

CH₂ —CH₃

TABLE 7 (Ig)

X⁴ _(r) R¹² Y² 2,4-Cl₂

O 4-Cl

O 4-Br —C(CH₃)₃ O — —C(CH₃)₃ O 4-C(CH₃)₃ —C(CH₃)₃ O 2-Cl —C(CH₃)₃ O 3-Cl—C(CH₃)₃ O 4-F —C(CH₃)₃ O

—C(CH₃)₃ O

—C(CH₃)₃ O 2,4-Cl₂ —C(CH₃)₃ O 2-CH₃, 4-Cl —C(CH₃)₃ O 3,4-(CH₃)₂ —C(CH₃)₃O 2,4,5-Cl₃ —C(CH₃)₃ O 4-Cl —CH₃ O 4-Cl

O 4-CF₃ —C(CH₃)₃ O 4-OCF₃ —C(CH₃)₃ O 2-OCHF₂ —C(CH₃)₃ O 4-OCH₃ —C(CH₃)₃O 4-Cl

O 4-Cl

O 2,4-Cl₂

CH₂ 4-Cl

CH₂ 4-Br —C(CH₃)₃ CH₂ — —C(CH₃)₃ CH₂ 4-C(CH₃)₃ —C(CH₃)₃ CH₂ 2-Cl—C(CH₃)₃ CH₂ 3-Cl —C(CH₃)₃ CH₂ 4-F —C(CH₃)₃ CH₂

—C(CH₃)₃ CH₂

—C(CH₃)₃ CH₂ 2,4-Cl₂ —C(CH₃)₃ CH₂ 2-CH₃, 4-Cl —C(CH₃)₃ CH₂ 3,4-(CH₃)₂—C(CH₃)₃ CH₂ 2,4,5-Cl₃ —C(CH₃)₃ CH₂ 4-Cl —CH₃ CH₂ 4-Cl

CH₂ 4-CF₃ —C(CH₃)₃ CH₂ 4-OCF₃ —C(CH₃)₃ CH₂ 2-OCHF₂ —C(CH₃)₃ CH₂ 4-OCH₃—C(CH₃)₃ CH₂ 4-Cl

CH₂ 4-Cl

CH₂ 4-Cl —C(CH₃)₃ O

TABLE 8 (Ih)

X⁵ _(s) A 2,4-Cl₂ —(CH₂)₃— 2,4-Cl₂ —(CH₂)₂— 4-Cl

4-CF₃

—CH₂—CH₂—

4-F

4-OCF₃

2,4-F₂

2-OCHF₂

—(CH₂)₃— 2,4,6-Cl₃

—

2,4-F₂

2,4-Cl₂

2,4-Cl₂

2,4-Cl₂

2,4-Cl₂

TABLE 9 (Ii)

X⁶ _(t) R¹³ 2,4-Cl₂ —CH₃ 2,4-Cl₂ —C₂H₅ 2,4-Cl₂ —CH(CH₃)₂ 4-Cl —C₃H₇-n2,4-Cl₂ —C₄H₉-n 2,4-Cl₂

2,4-Cl₂ —C(CH₃)₃ 2-Cl —C₃H₇-n 2-OCF₃ —C₃H₇-n 4-CF₃ —C₃H₇-n 4-CH₃ —C₃H₇-n2,4,6-Cl₃ —C₃H₇-n 2,4-Cl₂

4-F —C₃H₇-n 2,4-Cl₂

2,4-Cl₂

2,4-Cl₂

2,4-Cl₂

2,4-Cl₂

2,4-Cl₂

2,4-Cl₂

2,4-Cl₂

2,4-Cl₂

2,4-Cl₂

2,4-Cl₂ —CH₂—O—CF₂—CHF₂ 2,4-Cl₂ —CH₂—O—CF₂—CH₃ 4-Cl —CH₂—O—CF₂—CHF₂2,4-Cl₂ —CH₂—O—CF₃ 4-F —CH₂—O—CF₂—CHF₂ 2-Cl —CH₂—O—CF₂—CHF₂ 2,4-Cl₂—CH₂—CF₃ 2,4-Cl₂ —CF₂—CF₃ 2,4-Cl₂ —C₃H₇-n

TABLE 10 (Ik)

X⁷ _(u) R¹⁴ Y³ 2,4-Cl₂

O 4-Cl

O 4-Br —C(CH₃)₃ O — —C(CH₃)₃ O 4-C(CH₃)₃ —C(CH₃)₃ O 2-Cl —C(CH₃)₃ O 3-Cl—C(CH₃)₃ O 4-F —C(CH₃)₃ O

—C(CH₃)₃ O

—C(CH₃)₃ O 2,4-Cl₂ —C(CH₃)₃ O 2-CH₃, 4-Cl —C(CH₃)₃ O 3,4-(CH₃)₂ —C(CH₃)₃O 2,4,5-Cl₃ —C(CH₃)₃ O 4-Cl —CH₃ O 4-Cl

O 4-CF₃ —C(CH₃)₃ O 4-OCF₃ —C(CH₃)₃ O 2-OCHF₂ —C(CH₃)₃ O 4-OCH₃ —C(CH₃)₃O 4-Cl

O 4-Cl

O 2,4-Cl₂

CH₂ 4-Cl

CH₂ 4-Br —C(CH₃)₃ CH₂ — —C(CH₃)₃ CH₂ 4-C(CH₃)₃ —C(CH₃)₃ CH₂ 2-Cl—C(CH₃)₃ CH₂ 3-Cl —C(CH₃)₃ CH₂ 4-F —C(CH₃)₃ CH₂

—C(CH₃)₃ CH₂

—C(CH₃)₃ CH₂ 2,4-Cl₂ —C(CH₃)₃ CH₂ 2-CH₃, 4-Cl —C(CH₃)₃ CH₂ 3,4-(CH₃)₂—C(CH₃)₃ CH₂ 2,4,5-Cl₃ —C(CH₃)₃ CH₂ 4-Cl —CH₃ CH₂ 4-Cl

CH₂ 4-CF₃ —C(CH₃)₃ CH₂ 4-OCF₃ —C(CH₃)₃ CH₂ 2-OCHF₂ —C(CH₃)₃ CH₂ 4-OCH₃—C(CH₃)₃ CH₂ 4-Cl

CH₂ 4-Cl

CH₂ 4-Cl —C(CH₃)₃ O

TABLE 11 (Im)

X⁸ _(v) R¹⁵ 4-Cl —C₄H₉-n 2-Cl —C₄H₉-n 2,4-Cl₂ —C₄H₉-n 4-Br —C₄H₉-n 4-F—C₄H₉-n 4-C(CH₃)₃ —C₄H₉-n

—C₄H₉-n 4-Cl —C(CH₃)₃ 2-Cl —C(CH₃)₃ 2,4-Cl₂ —C(CH₃)₃ 2,4,6-Cl₃ —C(CH₃)₃4-CF₃ —C(CH₃)₃ 2-OCHF₂ —C(CH₃)₃ 4-Cl

4-Cl

4-Cl

4-Cl

4-Cl

4-Cl

—

—

Using 2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-olas starting material and iodine as oxidizing agent, the course of theprocess according to the invention can be illustrated by the equationbelow.

The formula (II) provides a general definition of the mercapto-triazolesrequired as starting materials for carrying out the process according tothe invention. In this formula, R¹ preferably has those meanings whichhave already been mentioned in connection with the description of thesubstances of the formula (I) according to the invention as beingpreferred for this radical.

Only some of the mercapto-triazoles of the formula (II) are known. Theycan be prepared by reacting triazoles of the formula

in which

R¹ is as defined above

either

α) successively with strong bases and sulphur in the presence of adiluent, followed by hydrolysis with water, if appropriate in thepresence of an acid,

or

β) with sulphur in the presence of a high-boiling diluent, followed, ifappropriate, by treatment with water and, if appropriate, with acid.

The formula (III) provides a general definition of the triazolesrequired as starting materials for carrying out the process forpreparing mercapto-triazoles of the formula (II). In the formula (III),R¹ preferably has those meanings which have already been mentioned inconnection with the description of the substances of the formula (I)according to the invention as being preferred for this radical.

The triazoles of the formula (III) are known or can be prepared by knownmethods (cf. EP-A 0 015 756, EP-A 0 040 345, EP-A 0 052 424, EP-A 0 061835, EP-A 0 297 345, EP-A 0 094 564, EP-A 0 196 038, EP-A 0 267 778,EP-A 0 378 953, EP-A 0 044 605, EP-A 0 069 442, EP-A 0 055 833, EP-A 0301 393, DE-A 2 324 010, DE-A 2 737 489, DE-A 2 551 560, EP-A 0 065 485,DE-A 2 735 872, EP-A 0 234 242, DE-A 2 201 063, EP-A 0 145 294 and DE-A3 721 786).

Suitable bases for carrying out the above process (α) for preparingmercaptotriazoles of the formula (II) are all strong alkali metal baseswhich are customary for such reactions. Preference is given to usingn-butyl-lithium, lithium diisopropyl-amide, sodium hydride, sodium amideand also potassium tert-butoxide in a mixture withtetramethylethylene-diamine (=TMEDA).

Suitable diluents for carrying out the above process (α) for preparingmercapto-triazoles of the formula (II) are all inert organic solventswhich are customarily used for such reactions. Preference is given tousing ethers, such as tetrahydrofuran, dioxane, diethyl ether and1,2-dimethoxyethane, furthermore liquid ammonia or else strongly polarsolvents, such as dimethyl sulphoxide.

Both when carrying out the above process (α) and the process (β),sulphur is preferably employed in the form of a powder.

When carrying out the above process (α), water, if appropriate in thepresence of an acid, is employed for hydrolysis. Suitable acids here areall inorganic or organic acids customary for such reactions. Preferenceis given to using acetic acid, dilute sulphuric acid and dilutehydrochloric acid. However, it is also possible to carry out thehydrolysis using aqueous ammonium chloride solution.

When carrying out the above process (α), the reaction temperatures canbe varied within a certain range. In general, the process is carried outat temperatures between −70° C. and +20° C., preferably between −70° C.and 0° C.

The above processes (α) and (β) are generally carried out underatmospheric pressure. However, it is also possible to operate underelevated or reduced pressure. Thus, in particular when carrying out theprocess (β), operation under elevated pressure may be suitable.

When carrying out the above process (α), generally 2 to 3 equivalents,preferably 2.0 to 2.5 equivalents, of strong base and subsequently anequivalent amount or else an excess of sulphur is employed per mole oftriazole of the formula (III). The reaction can be carried out under anatmosphere of protective gas, for example under nitrogen or argon.Work-up is carried out by customary methods. In general, the reactionmixture is extracted with an organic solvent which is sparingly solublein water, the combined organic phases are dried and concentrated and theresidue that remains is optionally purified by recrystallization and/orchromatography.

Suitable diluents for carrying out the above process (β) are allhigh-boiling organic solvents which are customary for such reactions.Preference is given to using amides, such as dimethylformamide anddimethylacetamide, furthermore heterocyclic compounds, such asN-methyl-pyrrolidone, and also ethers, such as diphenyl ether.

When carrying out the above process (β), a treatment with water and, ifappropriate, with acid can be carried out, if appropriate, after thereaction. This treatment is carried out like the hydrolysis in thepractice of the process (α).

When carrying out the above process (β), the reaction temperatures canalso be varied within a relatively large range. In general, the processis carried out at temperatures between 150° C. and 300° C., preferablybetween 180° C. and 250° C.

When carrying out the above process (β), generally 1 to 5 mol,preferably 1.5 to 3 mol, of sulphur are employed per mole of triazole ofthe formula (III). Work-up is carried out by customary methods. Ingeneral, the reaction mixture is extracted with an organic solvent whichis only sparingly soluble in water, the combined organic phases aredried and concentrated and the residue which remains is, if appropriate,freed of any impurities that may be present using customary methods,such as recrystallization or chromatography.

Suitable weak oxidizing agents for carrying out the process according tothe invention are all customary substances which are suitable for thegentle oxidation of organic compounds. Preference is given to usingiodine, air and hydrogen peroxide.

Suitable diluents for carrying out the process according to theinvention are all customary inert organic solvents and also water. Ifthe oxidizing agent used is iodine or air, preference is given to usingoptionally halogenated aliphatic, alicyclic or aromatic hydrocarbons,such as dichloromethane, chloroform, carbon tetrachloride,dichloroethane, trichloroethane, hexane, cyclohexane, benzene, toluene,xylene or chlorobenzene. If the oxidizing agent used is hydrogenperoxide, the diluent used is water in a mixture with an acid,preferably acetic acid.

When carrying out the process according to the invention, the reactiontemperatures can be varied within a certain range. In general, theprocess is carried out at temperatures between 0° C. and 50° C.,preferably between 10° C. and 40° C.

The process according to the invention is generally carried out underatmospheric pressure. However, it is also possible to operate underreduced or elevated pressure.

If appropriate, the process according to the invention is carried outunder an atmosphere of protective gas. Protective gases which arepreferred for this purpose are nitrogen or argon.

When carrying out the process according to the invention, in general anequivalent amount or else an excess of oxidizing agent is employed permole of mercapto-triazole of the formula (II). Work-up is carried out bycustomary methods. When working in an organic solvent, the reactionmixture is generally, if appropriate after prior extraction with anaqueous/alkaline solution, dried and concentrated under reducedpressure. If the diluent used is water in the presence of an acid, theresulting solid is generally separated off, washed and dried. Theproduct which is obtained in each case can, if appropriate, be freed ofany impurities that may be present by employing customary methods, forexample by recrystallization or chromatography.

The triazolyl disulphides of the formula (I) which are obtainable by theprocess according to the invention can be converted into acid additionsalts or metal salt complexes.

Suitable acids for the preparation of acid addition salts of thecompounds of the formula (I) are preferably those which have alreadybeen mentioned in connection with the description of the acid additionsalts according to the invention as being preferred acids.

The acid addition salts of the compounds of the formula (I) can beobtained in a simple manner by customary salt formation methods, forexample by dissolving a compound of the formula (I) in a suitable inertsolvent and adding the acid, for example hydrochloric acid, and they canbe isolated in a known manner, for example by filtering off, and, ifappropriate, purified by washing with an inert organic solvent.

Suitable salts for the preparation of metal salt complexes of thecompounds of the formula (I) are preferably those of metals which havealready been mentioned in connection with the description of the metalsalt complexes according to the invention as being preferred metalsalts.

The metal salt complexes of the compounds of the formula (I) can beobtained in a simple manner by customary processes, for example bydissolving the metal salt in alcohol, for example ethanol, and addingthe solution to the compounds of the formula (I). Metal salt complexescan be isolated in a known manner, for example by filtering off, and, ifappropriate, purified by recrystallization.

The active compounds according to the invention have strong microbicidalactivity and can be employed for controlling undesirable microorganisms,such as fungi and bacteria, in crop protection and in the protection ofmaterials.

In crop protection, fungicides are employed for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes, Deuteromycetes.

Some causative organisms of fungal and bacterial diseases which comeunder the generic names listed above may be mentioned as examples, butnot by way of limitation:

Xanthomonas species, such as Xanthomonas oryzae;

Pseudomonas species, such as Pseudomonas lachrymans;

Erwinia species, such as Erwinia amylovora;

Pythium species, such as Pythium ultimum;

Phytophthora species, such as Phytophthora infestans;

Pseudoperonospora species, such as Pseudoperonospora humuli orPseudoperonospora cubensis;

Plasmopara species, such as Plasmopara viticola;

Peronospora species, such as Peronospora pisi or P. brassicae;

Erysiphe species, such as Erysiphe graminis;

Sphaerotheca species, such as Sphaerotheca fuliginea;

Podosphaera species, such as Podosphaera leucotricha;

Venturia species, such as Venturia inaequalis;

Pyrenophora species, such as Pyrenophora teres or P. graminea (conidiaform: Drechslera, syn: Helminthosporium);

Cochliobolus species, such as Cochliobolus sativus (conidia form:Drechslera, syn: Helminthosporium);

Uromyces species, such as Uromyces appendiculatus;

Puccinia species, such as Puccinia recondita;

Tilletia species, such as Tilletia caries;

Ustilago species, such as Ustilago nuda or Ustilago avenae;

Pellicularia species, such as Pellicularia sasakii;

Pyricularia species, such as Pyricularia oryzae;

Fusarium species, such as Fusarium culmorum;

Botrytis species, such as Botrytis cinerea;

Septoria species, such as Septoria nodorum;

Leptosphaeria species, such as Leptosphaeria nodorum;

Cercospora species, such as Cercospora canescens;

Alternaria species, such as Alternaria brassicae and

Pseudocercosporella species, such as Pseudocercosporellaherpotrichoides.

The good toleration, by plants, of the active compounds, at theconcentrations required for controlling plant diseases, permitstreatment of above-ground parts of plants, of vegetative propagationstock and seeds, and of the soil.

The active compounds according to the invention are particularlysuitable for controlling Pyricularia oryzae and Pellicularia sasakii inrice and also for controlling cereal diseases, such asPseudocercosporella, Erysiphe species and Fusarium species. Thesubstances according to the invention can also be used effectivelyagainst Venturia and Sphaerotheca. Additionally, they also have verygood in vitro activity.

In materials protection the substances of the invention can be used toprotect industrial materials against infestation and destruction byundesirable microorganisms.

The term industrial materials in the present context refers to nonlivingmaterials which have been prepared for use in industry. Examples can beindustrial materials which are to be protected by novel activesubstances against microbial alteration or destruction, adhesives,sizes, paper and card, textiles, leather, wood, coating compositions andplastics articles, cooling lubricants and other materials which can beinfested or decomposed by microorganisms. In the context of thematerials to be protected mention may also be made of parts ofproduction plants, for example cooling water circuits, which may beadversely affected by reproduction of microorganisms. Preferredindustrial materials in the context of the present invention areadhesives, sizes, papers and cards, leather, wood, coating compositions,cooling lubricants and heat transfer fluids, especially wood.

Examples of microorganisms which can bring about degradation or analteration in the industrial materials are bacteria, fungi, yeasts,algae and slime organisms. The active substances according to theinvention preferably act against fungi, especially mould fungi,wood-discolouring and wood-destroying fungi (Basidiomycetes) and alsoagainst slime organisms and algae.

By way of example, mention may be made of the following genera:

Alternaria, such as Alternaria tenuis,

Aspergillus, such as Aspergillus niger,

Chaetomium, such as Chaetomium globosum,

Coniophora, such as Coniophora puetana,

Lentinus, such as Lentinus tigrinus,

Penicillium, such as Penicillium glaucum,

Polyporus, such as Polyporus versicolor,

Aureobasidium, such as Aureobasidium pullulans,

Sclerophoma, such as Sclerophoma pityophila,

Trichoderma, such as Trichoderma viride,

Escherichia, such as Escherichia coli,

Pseudomonas, such as Pseudomonas aeruginosa,

Staphylococcus, such as Staphylococcus aureus.

Depending on their respective physical and/or chemical properties, theactive substances can be converted into customary formulations, such assolutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols, very fine capsules in polymeric substances and in coatingcompositions for seed, and also ULV cold-mist and warm-mistformulations.

These formulations are prepared in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurface-active agents, that is, emulsifying agents and/or dispersingagents, and/or foam-forming agents. If the extender used is water, it isalso possible to employ, for example, organic solvents as auxiliarysolvents. Suitable liquid solvents are essentially: aromatics, such asxylene, toluene or alkylnaphthalenes, chlorinated aromatics orchlorinated aliphatic hydrocarbons, such as chlorobenzenes,chloroethylenes or methylene chloride, aliphatic hydrocarbons, such ascyclohexane or paraffins, for example mineral oil fractions, alcohols,such as butanol or glycol as well as their ethers and esters, ketones,such as acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanone, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, and also water; by liquefied gaseous extenders orcarriers are meant liquids which are gaseous at ambient temperature andunder atmospheric pressure, for example aerosol propellants, such asbutane, propane, nitrogen and carbon dioxide; as solid carriers thereare suitable: for example ground natural minerals, such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates; as solid carriers for granules there aresuitable: for example crushed and fractionated natural rocks such ascalcite, marble, pumice, sepiolite and dolomite, and also syntheticgranules of inorganic and organic meals, and granules of organicmaterial such as sawdust, coconut shells, maize cobs and tobacco stalks;as emulsifying and/or foam-forming agents there are suitable: forexample nonionic and anionic emulsifiers, such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonatesand also protein hydrolysates; as dispersing agents there are suitable:for example lignin-sulphite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, and also naturalphospholipids, such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations. Possible furtheradditives are mineral and vegetable oils.

It is possible to use colourants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, when used in cropprotection, can be used as such, or in their formulations also as amixture with known fungicides, bactericides, acaricides, nematicides orinsecticides, for example so as to widen the spectrum of action or toprevent the build up of resistance. In many cases, synergistic effectsare obtained, i.e. the efficacy of the mixture is higher than theefficacy of the individual components.

Suitable components for the mixtures are, for example, the followingsubstances:

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine;2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide;2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide;(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide;8-hydroxyquinoline sulphate; methyl(E)-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate;methyl (E)-methoxyimino[alpha-(o-tolyloxy)-o-tolyl]acetate;2-phenylphenol (OPP), aldimorph, ampropylfos, anilazine, azaconazole,benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol,blasticidin-S, bromuconazole, bupirimate, buthiobate, calciumpolysulphide, captafol, captan, carbendazim, carboxin, quinomethionate,chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb,cymoxanil, cypro-conazole, cyprofuram, dichlorophen, diclobutrazol,diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole,dimethirimol, dimethomorph, diniconazole, dinocap, diphenylaminc,dipyrithion, ditalimfos, dithianon, dodine, drazoxolon, edifenphos,epoxyconazole, ethirimol, etridiazole, fenarimol, fenbuconazole,fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentinacetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil,fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fthalide, fuberidazole,furalaxyl, furmecyclox, guazatine, hexachlorobenzene, hexaconazole,hymexazol, imazalil, imibenconazole, iminoctadine, iprobenfos (IBP),iprodione, isoprothiolane, kasugamycin, copper preparations such as:copper hydroxide, copper naphthenate, copper oxychloride, coppersulphate, copper oxide, oxine-copper and Bordeaux mixture, mancopper,mancozeb, maneb, mepanipyrim, mepronil, metalaxyl, metconazole,methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil, nickeldimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, ofurace,oxadixyl, oxamocarb, oxycarboxin, pefurazoate, penconazole, pencycuron,phosdiphen, pimaricin, piperalin, polyoxin, probenazole, prochloraz,procymidone, propamocarb, propiconazole, propineb, pyrazophos,pyrifenox, pyrimethanil, pyroquilon, quintozene (PCNB), sulphur andsulphur preparations, tebuconazole, tecloftalam, tecnazene,tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram,tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide,trichiamide, tricyclazole, tridemorph, triflumizole, triforine,triticonazole, validamycin A, vinclozolin, zineb, ziram.

Bactericides

bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,kasugamycin, octhilinone, furanecarboxylic acid, oxytetracyclin,probenazole, streptomycin, tecloftalam, copper sulphate and other copperpreparations.

Insecticides/acaricides/nematicides

abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb,alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A,azinphos M, azocyclotin, Bacillus thuringiensis, bendiocarb,benfuracarb, bensultap, beta-cyfluthrin, bifenthrin, BPMC, brofenprox,bromophos A, bufencarb, buprofezin, butocarboxim, butylpyridaben,cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap,CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrilos M,cis-resmethrin, clocythrin, clofentezine, cyanophos, cycloprothrin,cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,deltamethrin, demeton-M, demeton-S, denieton-S-methyl, diafenthiuron,diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion,diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton,edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox,ethoprophos, etrimphos, fenamiphos, fenazaquin, fenbutatin oxide,fenitrothion, fenobucarb, fenothiocarb, fenoxycarb, fenpropathrin,fenpyrad, fenpyroximate, fenthion, fenvalerate, fipronil, fluazinam,flucycloxuron, flucythrinate, fiufenoxuron, flufenprox, fluvalinate,fonophos, formothion, fosthiazate, fubfenprox, furathiocarb, HCH,heptenophos, hexaflumuron, hexythiazox, imidacloprid, iprobenfos,isazophos, isofenphos, isoprocarb, isoxathion, ivemectin,lambda-cyhalothrin, lufenuron, malathion, mecarbam, mervinphos,mesulfenphos, metaldehyde, methacrifos, methamidophos, methidathion,methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin,naled, NC 184, NI 25, nitenpyram, omethoate, oxamyl, oxydemethon M,oxydeprofos, parathion A, parathion M, permethrin, phenthoate, phorate,phosalone, phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M,pirimiphos A, profenofos, promecarb, propaphos, propoxur, prothiofos,prothoate, pymetrozin, pyrichlophos, pyridaphenthion, pyresmethrin,pyrethrum, pyridaben, pyrimidifen, pyriproxifen, quinalphos, RH 5992,salithion, sebufos, silafluofen, sulfotep, sulprofos, tebufenozid,tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, temephos,terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, thiofanox,thiomethon, thionazin, thuringiensin, tralomethrin, triarathen,triazophos, triazuron, trichlorfon, triflumuron, trimethacarb,vamidothion, XMC, xylylcarb, zetamethrin.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, is also possible.

The active compounds can be used as such or in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, emulsifiable concentrates, emulsions, foams, suspensions,wettable powders, pastes, soluble powders, dusts and granules. They areused in the customary manner, for example by watering, spraying,atomizing, scattering, dusting, foaming, brushing on and the like. It isfurthermore possible to apply the active compounds by the ultra-lowvolume method or to inject the active compound formulation or the activecompound itself into the soil. The seeds of the plants can also betreated.

In the treatment of parts of plants, the concentrations of activesubstance in the use forms can be varied within a relatively largerange: they are in general between 1 and 0.0001% by weight, preferablybetween 0.5 and 0.001% by weight.

In the treatment of seed, amounts of active substance of from 0.001 to50 g per kilogram of s eed, preferably from 0.01 to 10 g, are generallyrequired.

In the case of the treatment of soil, active-substance concentrations offrom 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% byweight, are required at the site of action.

The compositions used for protecting industrial materials comprise theactive substances in an amount of in general from 1 to 95%, preferablyfrom 10 to 75%.

The concentrations in which the novel active substances are applieddepend on the nature and on the incidence of the microorganisms to becontrolled and on the composition of the material to be protected. Theoptimum amount for use can be determined by means of test series. Ingeneral, the use concentrations are in the range from 0.001 to 5% byweight, preferably from 0.05 to 1.0% by weight, based on the material tobe protected.

The effectiveness and the spectrum of action of the active substances tobe used in materials protection in accordance with the invention and ofthe compositions, concentrates or, very generally, formulations whichcan be prepared therefrom can be increased by adding, if desired,further antimicrobially active compounds, fungicides, bactericides,herbicides, insecticides or other active substances to increase thespectrum of action or to achieve particular effects, for exampleadditional protection against insects. These mixtures may possess abroader spectrum of action than the compounds according to theinvention.

The preparation and the use of the substances according to the inventionis illustrated by the examples below.

Preparation Examples Example 1

Variant a:

At room temperature and under an atmosphere of nitrogen, a mixture of3.42 g (10 mmol) of2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-oland 1.27 g (0.01 g atom) of iodine in 50 ml of absolute dichloromethaneis stirred for 46 hours. The reaction mixture is subsequently extractedwith saturated aqueous sodium carbonate solution and then dried oversodium sulphate. The organic phase is concentrated under reducedpressure. In this manner, 3.3 g (96% of theory) ofdi-{1-[2-(1-chlorocyclopropyl)-3-(2-chloro-phenyl)-2-hydroxy-propyl-1]-1,2,4-triazol-5-yl}disulphide are obtained in the form of a solid substance of meltingpoint 128 to 131° C.

¹H NMR spectrum (200 MHz; CDCl₃; TMS): δ=0.4-1.0 (m,8H); 3.05 (d,2H);3.7 (d,2H); 3.95 (2d,2H); 4.3 (s, 2OH); 5.05 (d, 2H); 7.2-7.6 (m,8H);8.0 (s,2H) ppm

Variant b

At room temperature, a mixture of 1.7 g (5 mmol) of2-(1-chlorocyclopropyl)-1-(2-chloro-phenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol,25 ml of water and 0.6 g (10 mmol) of acetic acid is admixed with 1.1 ml(10 mmol) of 35% strength hydrogen peroxide and stirred at roomtemperature for 96 hours. The precipitated solid product is filtered offwith suction, washed with water and dried under reduced pressure. Inthis manner, 1.7 g (100% of theory) ofdi-{1-[2-(1-chloro-cyclopropyl)-3-(2-chloro-phenyl)-2-hydroxy-propyl-1]-1,2,4-triazol-5-yl}disulphide are obtained in the form of a solid substance of meltingpoint 129 to 131° C.

Example 2

The compound of the above formula is prepared from the mercapto-triazoleof the formula (II17) using the method given in Example 1.

¹H NMR spectrum (200 MHz; CDCl₃; TMS): δ=4.5 (d,1H); 4.9 (d,1H); 5.6(s,1H); 6.7-7.4 (m,8H); 7.8 (s,1H) ppm

Preparation of Starting Materials Example 3

Variant α

At −20° C., a mixture of 3.12 g (10 mmol) of2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-oland 45 ml of absolute tetrahydrofuran is admixed with 8.4 ml (21 mmol)of n-butyl-lithium in hexane and stirred at 0° C. for 30 minutes. Thereaction mixture is subsequently cooled to −70° C., admixed with 0.32 g(10 mmol) of sulphur powder and stirred at −70° C. for 30 minutes. Themixture is warmed to −10° C., admixed with ice-water and adjusted to pH5 by addition of dilute sulphuric acid. The mixture is extractedrepeatedly with ethyl acetate and the combined organic phases are driedover sodium sulphate and concentrated under reduced pressure. In thismanner, 3.2 g (93% of theory) of2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-olare obtained in the form of a solid substance which, afterrecrystallization, melts at 138-139° C.

Variant β

With stirring, a mixture of 3.12 g (10 mmol) of2-(1-chloro-cyclopropyl)-1-(2-chloro-phenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol,0.96 g (30 mmol) of sulphur powder and 20 ml of absoluteN-methyl-pyrrolidone is heated at 200° C. for 44 hours. The reactionmixture is subsequently concentrated under reduced pressure (0.2 mbar).The resulting crude product (3.1 g) is recrystallized from toluene. Inthis manner, 0.7 g (20% of theory) of2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-olis obtained in the form of a solid substance of melting point 138-139°C.

Example 4

At −70° C., a mixture of 1.41 g (5 mmol) of1,2-dichloro-4,4-dimethyl-5-fluoro-3-hydroxy-3-[(1,2,4-triazol-1-yl)-methyl]-1-penteneand 25 ml of absolute tetrahydrofuran is admixed with 4 ml (10 mmol) ofn-butyl-lithium in hexane and stirred at −70° C. for one hour. Thereaction mixture is then admixed with 0.19 g (6 mmol) of sulphur powderand stirred at −70° C. for 4 hours. The mixture is subsequentlyhydrolysed at −70° C. by addition of 1 ml of methanol and 1 ml of aceticacid. The reaction mixture is initially diluted with ethyl acetate andthen extracted repeatedly with saturated aqueous ammonium chloridesolution. The organic phase is dried over sodium sulphate andconcentrated under reduced pressure. The resulting crude product (1.7 g)is purified by silica gel chromatography using a mixture of petroleumether and ethyl acetate =1:1 as mobile phase. In this manner, 0.5 g (32%of theory) of1,2-dichloro-4,4-dimethyl-5-fluoro-3-hydroxy-3-[(5-mercapto-1,2,4-triazol-1-yl)-methyl]-1-penteneis obtained in the form of a solid substance of melting point 162-164°C.

The compounds listed in Table 13 below are also prepared using themethods given in Examples 2 and 3.

TABLE 12 (II-b)

Ex. No. Comp. No. R² R³ Physical constant 5 (II-3) —CCl═CHCl —C(CH₃)₃m.p. 168-169° C. 6 (II-4)

GC/MS (Cl):376 (M + H⁺) 7 (II-5)

m.p. 163-164° C. 8 (II-6)

—C(CH₃)₃ m.p. 127° C. 9 (II-7)

Oil 10 (II-8)

GC/MS (Cl):340 (M + H⁺) 11 (II-9)

GC/MS (Cl):424 (M + H⁺) 12 (II-10)

m.p. 168° C. 13 (II-11)

GC/MS (Cl):314 (M + H⁺) 14 (II-12)

GC/MS (Cl):346 (M + H⁺) 15 (II-13)

m.p. 115-118° C. 16 (II-14)

—C(CH₃)₃ GC/MS (Cl):340 (M + H⁺) 17 (II-15)

GC/MS (Cl):334 (M + H⁺) 18 (II-16)

—C₄H₉-n *) *)The compound is characterized by the following signals inthe ¹H NMR spectrum (400 MHz, CDCl₃/TMS): δ = 0.8(t, 3H); 0.85(m, 2H);1.25(m, 2H); 1.8(m, 1H); 2.55(m, 1H); 4.6(OH); 4.9(AB, 2H); 7.2(dd, 1H);7.35(d, 1H); 7.7(s, 1H); 7.75(d, 1H); 12.3(5H) ppm

The compound is characterized by the following signals in the ¹H NMRspectrum (400 MHz, CDCl₃/TMS): δ=0.8 (t, 3H); 0.85 (m, 2H); 1.25 (m,2H); 1.8 (m, 1H); 2.55 (m, 1H); 4.6 (OH); 4.9 (AB, 2H); 7.2 (dd, 1H);7.35 (d, 1H); 7.7 (s, 1H); 7.75 (d, 1H); 12.3 (5H) ppm

Example 19

At −70° C., a mixture of 1.3 g (4 mmol) of3-(2-chloro-phenyl)-2-(4-fluoro-phenyl)-2-(1,2,4-triazol-1-yl-methyl)-oxirane(Z form) and 25 ml of absolute tetrahydrofuran is admixed with 2.0 ml (5mmol) of n-butyl-lithium in hexane and stirred at −70° C. for 1 hour.The reaction mixture is then admixed with 0.16 g (5 mmol) of sulphurpowder and stirred at −70° C. for 4 hours. Subsequently, 1 ml ofmethanol and 1 ml of acetic acid are simultaneously added dropwise withstirring at −70° C. The resulting mixture is diluted withdichloromethane and extracted repeatedly with saturated aqueous ammoniumchloride solution. The organic phase is dried over sodium sulphate andthen concentrated under reduced pressure. The resulting crude product(1.9 g) which, according to the gas chromatogram, contains 51.0% of thedesired product, in addition to 20.7% of starting material, isrecrystallized from toluene. In this manner, 0.8 g (55% of theory) of3-(2-chlorophenyl)-2-(4-fluoro-phenyl)-2-(5-mercapto-1,2,4-triazol-1-yl-methyl)-oxirane(Z form) is obtained as a solid substance of melting point 179 to 180°C.

¹H NMR spectrum (200 MHz, CDCl₃, TMS): δ=3.7 (d, J=15 Hz, 1H); 4.1 (s,1H); 5.15 (d, J=15 Hz, 1H); 6.95-7.6 (m, 8H); 7.65 (s, 1H); 11.0 (s, 1H)ppm.

GC/MS (ci): 362 (M+H⁺)

Example 20

At −20° C., a mixture of 1.6 g (5 mmol) of5-(4-chlorobenzyl)-2,2-dimethyl-l-(1,2,4-triazol-1-yl-methyl)-cyclopentane-1-ol(Z form) and 30 ml of absolute tetrahydrofuran is admixed with 4 ml (10mmol) of n-butyl-lithium in hexane, and stirring is continued at 0° C.for 30 minutes. The reaction mixture is subsequently cooled to −70° C.,admixed with stirring with 0.19 g (6 mmol) of sulphur powder and thenstirred at −70° C. for 1 hour and subsequently at 0° C. for 2 hours, Theresulting mixture is diluted with ethyl acetate and extracted repeatedlywith saturated aqueous ammonium chloride solution. The organic phase isdried over sodium sulphate and then concentrated under reduced pressure.The resulting crude product (2.0 g) is recrystallized from toluene. Inthis manner, 1.1 g (63% of theory) of 5-(4-chloro-benzyl)-2,2-dimethyl-1-(5-mercapto-1,2,4-triazol-1-yl-methyl)-cyclopentan-1-ol (Z form) areobtained as a solid substance of melting point 179 to 180° C.

GC/MS (ci): 352 (M+H⁺)

Example 21

At −20° C., a mixture of 1.59 g (5 mmol) of2-(4-chloro-benzylidene)-5,5-dimethyl-1-(1,2,4-triazol-1-yl-methyl)-cyclopentan-1-oland 30 ml of absolute tetrahydrofuran is admixed with 4.4 ml (11 mmol)of n-butyl-lithium in hexane, and stirring is continued at 0° C. for 30minutes. The reaction mixture is subsequently cooled to −70° C., admixedwith stirring with 0.19 g (6 mmol) of sulphur powder and then stirred at−70° C. for 1 hour and subsequently at 0° C. for 2 hours. The resultingmixture is diluted with ethyl acetate and extracted repeatedly withsaturated aqueous ammonium chloride solution. The organic phase is driedover sodium sulphate and then concentrated under reduced pressure. Theresulting crude product (1.9 g) is chromatographed over silica gel usingethyl acetate. In this manner, 0.8 g (46% of theory) of2-(4-chloro-benzylidene)-5,5-dimethyl-1-(5-mercapto-1,2,4-triazol1-yl-methyl)-cyclopentan-1-olis obtained.

¹H-NMR spectrum (200 MHz, CDCl₃; TMS): δ=0.9 (s,3H); 1.15 (s,3H);1.6-1.95 (m,2H); 2.4-3.0 (m,2H); 4.25 (d,1H); 4.55 (d,1H); 5.9 (m,1H);7.1-7.3 (m,4H); 7.6 (s,1H) ppm

Example 22

At −20° C., a mixture of 1.53 g (5 mmol) of2-(2,4-difluoro-phenyl)-1,3-bis-(1,2,4-triazol--1-yl)-propan-2-ol and 30ml of absolute tetrahydrofuran is admixed with 4.4 ml (11 mmol) ofn-butyl-lithium in hexane, and stirring is continued at 0° C. for 30minutes. The reaction mixture is subsequently cooled to −70° C., admixedwith stirring with 0.19 g (6 mmol) of sulphur powder and then stirred at−70° C. for 1 hour and subsequently at 0° C. for 2 hours. The resultingmixture is diluted with ethyl acetate and extracted repeatedly withsaturated aqueous ammonium chloride solution. The organic phase is driedover sodium sulphate and then concentrated under reduced pressure. Theresulting crude product (2.3 g) is purified by silica gel chromatographyusing a mixture of ethyl acetate and ethanol=9:1 as mobile phase. Inthis manner, 1.0 g (59% of theory) of2-(2,4-difluoro-phenyl)-1-(5-mercapto-1,2,4-triazol-1-yl)-3-(1,2,4-triazol-1-yl)-propan-2-olis obtained in the form of a solid substance of melting point 187° C.

GC/MS (ci): 339 (M+H⁺)

Example 23

At −20° C., a mixture of 1.72 g (5 mmol) of2,2-dimethyl-3-hydroxy-4-(1,2,4-triazol-1-yl)-1-(4-trifluoromethoxy-phenyl)-pentaneand 30 ml of absolute tetrahydrofuran is admixed with 4.4 ml (11 mmol)of n-butyl-lithium in hexane, and stirring is continued at 0° C. for 30minutes. The reaction mixture is subsequently cooled to −70° C., admixedwith stirring with 0.19 g (6 mmol) of sulphur powder and then stirred at−70° C. for 1 hour and subsequently at 0° C. for 2 hours. The resultingmixture is diluted with ethyl acetate and extracted repeatedly withsaturated aqueous ammonium chloride solution. The organic phase is driedover sodium sulphate and then concentrated under reduced pressure. Theresulting crude product (2.2 g) is purified by silica gel chromatographyusing a mixture of petroleum ether and ethyl acetate=1:1 as mobilephase. In this manner, 1.4 g (75% of theory) of2,2-dimethyl-3-hydroxy-4-(5-mercapto-1,2,4-triazol-1-yl)-1-(4-trifluoromethoxy-phenyl)-pentaneare obtained in the form of a solid substance of melting point 125 to126° C.

GC/MS(ci): 376 (M+H⁺)

Example 24

At −20° C., a mixture of 1.48 g (5 mmol) of1-(4-chloro-phenoxy)-1-(1,2,4-triazol-1-yl)-3,3-dimethyl-butan-2-ol and30 ml of absolute tetrahydrofuran is admixed with 4 ml (10 mmol) ofn-butyl-lithium in hexane, and stirring is continued at −20° C. for 30minutes. At −20° C., the reaction mixture is then admixed with stirringwith 0.19 g (6 mmol) of sulphur powder and then stirred at −20° C. for 1hour and subsequently at 0° C. for 2 hours. The resulting mixture isdiluted with ethyl acetate and extracted repeatedly with saturatedaqueous ammonium chloride solution. The organic phase is dried oversodium sulphate and then concentrated under reduced pressure. Theresulting crude product (1.9 g) is purified by silica gel chromatographyusing a mixture of petroleum ether and ethyl acetate=1:1 as mobilephase. In this manner, 0.7 g (43% of theory) of1-(4-chlorophenoxy)-1-(5-mercapto-1,2,4-triazol-1-yl)-3,3-dimethyl-butan-2-olis obtained in the form of a solid substance of melting point 193 to194° C.

MS(ci): 328 (M+H⁺)

Example 25

With stirring, a mixture of 2.0 g (5 mmol) of2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-(1,2,4-triazol-1-ylmethyl)-4-methyl-1,3-dioxolan,0.32 g (10 mmol) of sulphur powder and 10 ml of absoluteN-methylpyrrolidone is heated at 200° C. for 22 hours. The reactionmixture is subsequently concentrated under reduced pressure (0.2 mbar).The remaining residue is admixed with ethyl acetate, and the resultingmixture is extracted repeatedly with saturated aqueous ammonium chloridesolution. The organic phase is dried over sodium sulphate and thenconcentrated under reduced pressure. The resulting crude product (1.8 g)is purified by silica gel chromatography using a mixture of petroleumether and ethyl acetate=1:1 as mobile phase. In this manner, 0.9 g (41%of theory) of2-[2-chloro-4-(4-chloro-phenoxy)-phenyl]-2-[(5-mercapto-1,2,4-triazol-1-yl)-methyl]-4-methyl-1,3-dioxolanis obtained in the form of an isomer mixture.

MS (ci): 438 (M+H⁺, 100%)

Example 26

Under an atmosphere of nitrogen and with stirring, a mixture of 1.42 g(5 mmol) of 2-(2,4-dichloro-phenyl)-1-(1,2,4-triazol-1-yl)-pentane, 0.32g (10 mmol) of sulphur powder and 10 ml of absolute N-methylpyrrolidoneis heated at 200° C. for 3 hours. The reaction mixture is subsequentlyconcentrated under reduced pressure. The residue that remains is admixedwith ethyl acetate, and the resulting mixture is extracted repeatedlywith saturated aqueous ammonium chloride solution. The organic phase isdried over sodium sulphate and then concentrated under reduced pressure.The resulting crude product (2.1 g) is purified by silica gelchromatography using a mixture of petroleum ether and ethyl acetate=1:1as mobile phase. In this manner, 1.5 g (95% of theory) of2-(2,4-dichloro-phenyl)-1-(5-mercapto-1,2,4-triazol-1-yl)-pentane areobtained in the form of a solid substance of melting point 103° C.

Example 27

Under an atmosphere of nitrogen and with stirring, a mixture of 2.93 g(10 mmol) of1-(4-chloro-phenoxy)-1(1,2,4-triazol-1-yl)-3,3-dimethyl-butan-2-one,0.64 g (20 mmol) of sulphur powder and 10 ml of absoluteN-methylpyrrolidone is heated at 200° C. for 8 hours. The reactionmixture is subsequently concentrated under reduced pressure and theresidue that remains is dissolved in dichloromethane. The resultingmixture is extracted repeatedly with saturated aqueous ammonium chloridesolution.

The organic phase is dried over sodium sulphate and then concentratedunder reduced pressure. The resulting crude product (2.7 g) is purifiedby silica gel chromatography using a mixture of petroleum ether andethyl acetate=1:1 as mobile phase. In this manner, 2.0 g (62% of theory)of1-(4-chlorophenoxy)-1-(5-mercapto-1,2,4-triazol-1-yl)-3,3-dimethyl-butan-2-oneare obtained in the form of a solid substance of melting point 134 to136° C.

Example 28

Under an atmosphere of nitrogen and with stirring, a mixture of 1.68 g(5 mmol) of4-(4-chloro-phenyl)-2-cyano2-phenyl-1-(1,2,4-triazol-1-yl)-butane, 0.32g (10 mmol) of sulphur powder and 10 ml of absolute N-methylpyrrolidoneis heated at 200° C. for 47 hours. The reaction mixture is subsequentlyconcentrated under reduced pressure, and the residue that remains isdissolved in ethyl acetate. The resulting mixture is extractedrepeatedly with saturated aqueous ammonium chloride solution. Theorganic phase is dried over sodium sulphate and then concentrated underreduced pressure. The resulting crude product (1.9 g) is purified bysilica gel chromatography using a mixture of petroleum ether and ethylacetate=1:1 as mobile phase. In this manner, 0.7 g (38% of theory) of4-(4-chloro-phenyl)-2-cyano-2-phenyl-1-(5-mercapto-1,2,4-triazol-1-yl)butaneis obtained in the form of an oil.

¹H NMR spectrum (400 MHz, CDCl₃, TMS): δ=2.4 (m, 3H); 2.75 (m, 1H); 4.5(AB, 2H); 7.0 (d, 2H); 7.2 (d, 2H); 7.4 (m, 3H); 7.55 (m, 2H); 7.8 (s,1H); 11.7 (1H) ppm.

USE EXAMPLES Example A

Erysiphe Test (Barley)/Curative

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for curative activity, young plants are dusted with spores ofErysiphe graminis f.sp. hordei. 48 hours after the inoculation, theplants are sprayed with the preparation of active compound at the statedapplication rate.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a relative atmospheric humidity of approximately 80%, inorder to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE A Erysiphe test (barley)/curative Application rate of activecompound Active compound in g/ha Efficacy in % According to theinvention (I-1)

250 100

Example B

Erysiphe test (Barley)/Protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f.sp. hordei.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a relative atmospheric humidity of approximately 80%, inorder to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE B Erysiphe test (barley)/protective Application rate of activecompound in Efficacy in Active compound g/ha % According to theinvention (I-1)

250 100

Example C

Erysiphe Test (Wheat)/Protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are dusted with sporesof Erysiphe graminis f.sp. tritci.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a relative atmospheric humidity of approximately 80%, inorder to promote the development of mildew pustules.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE C Erysiphe test (wheat)/protective Application rate of activecompound in Active compound g/ha Efficacy in % According to theinvention (I-1)

250 100

Example D

Fusarium graminearum Test (Barley)/Protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are sprayed with aconidia suspension of Fusarium graminearum.

The plants are placed in a greenhouse under light-transparent incubationhoods at a temperature of approximately 20° C. and a relativeatmospheric humidity of approximately 100%.

Evaluation is carried out 4 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and tests results areshown in the table below.

TABLE D Fusarium graminearum test (barley)/protective Application rateof active compound in Efficacy in Active compound g/ha % According tothe invention (I-1)

250 100

Example E

Pseudocercosporella herpotrichoides Test; W Strain (Wheat/Protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are inoculated at thebase of the stem with spores of the W strain of Pseudocercosporellaherpotrichoides.

The plants are placed in a greenhouse at a temperature of approximately10° C. and a relative atmospheric humidity of approximately 80%.

Evaluation is carried out 21 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE E Pseudocercosporella herpotrichoides test; W strain(wheat)/protective Application rate of active Efficacy in Activecompound compound in g/ha % According to the invention (I-1)

250 100

Example F

Puccinia Test (Wheat/Curative

Solvent: 10 parts by weight of N-methyl-pyrrolidone

Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for curative activity, young plants are inoculated with a sporesuspension of Puccinia recondita in an aqueous 0.1% strength solution ofagar. The plants remain in an incubation cabin at 20° C. and 100%relative atmospheric humidity for 24 hours.

48 hours after the inoculation the plants are sprayed with thepreparation of active compound at the stated application rate.

The plants are placed in a greenhouse at a temperature of approximately20° C. and a relative atmospheric humidity of approximately 80%, inorder to promote the development of rust pustules.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE F Puccinia test (wheat)/curative Application rate of activeEfficacy in Active compound compound in g/ha % According to theinvention (I-1)

250 100

Example G

Sphaerotheca Test (Cucumber/Protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Sphaerotheca fuliginea.

The plants are subsequently placed in a greenhouse at 23 to 24° C. andat a relative atmospheric humidity of approximately 75%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE G Sphaerotheca test (cucumber)/protective Application rate ofactive compound in Efficacy in Active compound g/ha % According to theinvention (I-1)

50 100 (I-2)

50  92

Example H

Podosphaera Test (Apple)/Protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are inoculated with anaqueous spore suspension of the causative organism of apple mildewPodosphaera leucotricha.

The plants are then placed in a greenhouse at 23° C. and at a relativeatmospheric humidity of approximately 75%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE H Podosphaera test (apple)/protective Application rate of activecompound Efficacy in Active compound in g/ha % According to theinvention (I-1)

50 100 (I-2)

50  96

Example I

Venturia Test (Apple)/Protective

Solvent: 47 parts by weight of acetone

Emulsifier: 3 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate.

After the spray coating has dried on, the plants are inoculated with anaqueous conidia suspension of the causative organism of apple scabVenturia inaequalis and then remain placed at 20° C. and a relativeatmospheric humidity of approximately 70% for 1 day.

The plants are then placed in a greenhouse at 20° C. and at a relativeatmospheric humidity of approximately 70%.

Evaluation is carried out 12 days after the inoculation. 0% means anefficacy which corresponds to that of the control, while an efficacy of100% means that no infection is observed.

Active compounds, active compound concentrations and test results areshown in the table below.

TABLE I Venturia test (apple)/protective Application rate of activecompound in Active compound g/ha Efficacy in % According to theinvention (I-1)

50 100

What is claimed is:
 1. A triazolyl disulphide of the formula (I)

wherein R¹ represents a radical of the formula

R⁶ and R⁷ independently of one another each represents hydrogen or alkylhaving 1 to 6 carbon atoms, X¹ represents halogen, alkyl having 1 to 5carbon atoms, alkoxy having 1 to 4 carbon atoms, phenyl, phenoxy,halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms,halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms orrepresents halogenoakylthio having 1 to 4 carbon atoms and 1 to 5halogen atoms, and m represents the numbers 0, 1 or
 2. 2. A microbicidalcomposition comprising a microbicidally effective amount of thetriazolyl disulphide of claim 1 and a member selected from the groupconsisting of extenders, surfactants and mixtures thereof.
 3. A methodof controlling undesirable microorganisms in crop protection and in theprotection of materials comprising applying a microbicidally effectiveamount of the triazolyl disulphide of claim 1 to the microorganismsand/or their habitat.
 4. The triazolyl disulphide of claim 1, wherein R⁶and R⁷ each represent methyl, m represents 1, and X¹ represents 4-Cl.